Jackson returned to Baylor for his senior season in 2012–13. He was named the Big 12 preseason Player of the Year[3] and was named to the preseason watch lists for the Wooden[4] and Naismith[5] national player of the year awards.

On April 4, 2013, Jackson ended his college career with a championship win over Iowa at the National Invitation Tournament (NIT). As a senior, he averaged 19.8 points and 7.1 assists per game.

On July 27, 2013, Jackson signed a one-year deal with ASVEL Villeurbanne of the LNB Pro A.[8] However, he left the team in September 2013 before appearing in a game for them.[9]

On November 1, 2013, Jackson was selected with the fourth overall pick in the 2013 NBA D-League draft by the Idaho Stampede.[10] On February 3, 2014, he was named to the Futures All-Star roster for the 2014 NBA D-League All-Star Game.[11][12] On February 4, 2014, he scored 58 points against the Texas Legends, setting the D-League single-game scoring record. This surpassed the previous record of 53 by Morris Almond (2008) and Will Conroy (2009).[13][14]

On February 20, 2014, Jackson left the Idaho Stampede in order to sign in Turkey.[15] The next day, he signed with Fenerbahçe Ülker for the rest of the 2013–14 season.[16] On April 10, 2014, he parted ways with Fenerbahçe after just six games.[17] He averaged 3.3 points and 1.3 assists over those six games.

On June 27, 2014, the Pelicans traded Jackson's rights back to the Philadelphia 76ers in exchange for Russ Smith's draft rights.[18] On July 1, 2014, he joined the 76ers for the 2014 NBA Summer League.[19] In game one of the 76ers' Orlando Summer League schedule on July 5, he ruptured his right Achilles during the first half of their 77-83 loss to the Orlando Magic.[20][21] Despite the injury, he signed a one-year, partially guaranteed contract with the 76ers on July 24, 2014,[22] only to be waived on September 30 after he was ruled out for six to 12 months.[23]

On July 15, 2015, Jackson re-signed with the 76ers after averaging 12 points per game in two Las Vegas Summer League games.[24] However, he was later waived by the 76ers on October 26 after appearing in three preseason games.[25]

On January 6, 2016, Jackson was reacquired by the Idaho Stampede.[26] He made his season debut for the Stampede three days later in a 98–92 win over the Fort Wayne Mad Ants, recording six points, one rebound, two assists and one steal in 11 minutes of action off the bench.[27] On March 4, he was traded to the Texas Legends in exchange for the returning player rights to Eric Griffin.[28] On March 20, he waived by the Legends before appearing in a game for them.[29]

On November 30, 2016, Jackson was reacquired by the Texas Legends.[32] After appearing in 10 games for the Legends, he signed with the Dallas Mavericks on December 27, 2016.[33] That night, he made his NBA debut in a 123–107 loss to the Houston Rockets, recording seven points, one rebound and two assists in 11 minutes off the bench.[34] On January 6, 2017, he was waived by the Mavericks.[35] Two days later, he was reacquired by the Texas Legends.[36] He returned to the Mavericks on January 15, signing a 10-day contract with the team.[37] On January 25, he signed a second 10-day contract with the Mavericks.[38] He made his first career start in the Mavericks' game against the Oklahoma City Thunder on January 26, and recorded nine points, two rebounds and four assists in 13 minutes before leaving the game in the first half with a left hamstring strain.[39] He was subsequently waived two days later,[40] and immediately re-joined the Legends.[41] On February 6, 2017, he was named in the Western Conference All-Star team for the 2017 NBA D-League All-Star Game.[42]